“I fucked enough men for a small, sex-starved country.”

Dorothy Freed, an amazing 70-year-old sex maven and erotica writer, was coming of age 1950s and 60s, when quoting Sigmund Freud was all the rage. During our interview, she told me about some crazy beliefs from back then — beliefs that led to her sleeping with 100 different men in search of the penis that would give her a vaginal orgasm.

As smart he was, Freud had a tendency to get a little overconfident when it came to talking about women’s vaginas — and it had some gruesome consequences for women for the next 50 years or more.

You see, Freud wrote numerous essays stating that when a woman hits puberty, her erogenous zone moves from the clit to the vaginal wall. He also claimed that the best kind of orgasm was a simultaneous orgasm between man and woman, in which the woman comes from internal stimulation.

Whaaa whaaaat

I know. I know.

Basically, Freud was so emphatic about this, women all over the western world were thereby CONVINCED by the great psychologist that there was something wrong with them if they didn’t orgasm when a penis was going in and out of their vagina

* Read more about Freud at the bottom of the post

But back to our interviewee.

The whole P-in-V orgasm myth did not escape Dorothy, who was 16 when she had her first orgasm. It happened on the day she had borrowed her mother’s “neck massager.”

“That vibrator looked like a gun, with a gun-type handle and three things (one like a cup, one that was flat and one with several nubs) that screwed onto a vibrating metal disk.”

Dorothy “accidentally dropped” the massager into her lap and POW just like that, “I came so hard my legs buckled. Just, over and over and over and over again. I thought, wow! I wonder what my mom does with this? I had a feeling she probably massaged her neck, like she said,” Dorothy told me with a smile.

So there it was, Dorthy could come, and how, with a vibrator. But according to the common mistruth of the era, that was like, nice and all for little girls, but real women came when a penis was inside them, not from vibrators.

So Dorothy got married at 17, to the first guy who showed her his cock. Sex with her first husband kind of sucked, in part because he was always pressuring her to come from P-in-V sex.

“I once confessed to my idiot husband that I masturbated with a vibrator. He said, patronizingly, ‘That’s ok,’ because I would learn to do it ‘properly’ afterwards. But he never really gave me enough time. And I have a very small clit.”

“It was rare but sometimes he would eat me. But most of the time he considered that a warm up for the ‘real thing.’

Then when we’d be having sex, he would hover over me, waiting for me to come. Because in the 60s it HAD to be simultaneous. So he’d go, ‘Are ya close yet? Are ya close yet?’ And that little whisper would freeze my blood, ending any chance I had of coming. Because when you’re timing it, it’s pretty scary. So I faked it. And I hated him for it and I hated me.”

I’ll get into this more in part II of Dorothy’s interview, but after more than a decade of marriage, Dorothy left her husband after finding him in bed with one of her best friends.

Then she moved to San Francisco and proceeded to sleep with 100 or so men over the course of the decade, searching for the penis that could bring her to mythical, vaginal, orgasmic bliss. Really, 100.

“I had fucked enough men for a small, sex-starved country,” she said.

But guess what? After all that fucking, it still didn’t happen for her.

Dorothy had a realization that her quest was misguided. It happened, as so many important realizations do, at an orgy. There were people on top of other people, banging every which way imaginable. And after some quality menage a cent, she excused herself to go to the bathroom.

It was there, in the dimly-lit bathroom that she washed her hands, looked into her own eyes and asked, “Am I even having fun anymore?”

And really, she wasn’t.

So Dorothy left the orgy that night with a new plan in mind. Soon after, she adopted her first dog. That made it easier to stay at home alone. She began painting more and working on her art. She stopped trying to fuck every promising penis in sight and decided that maybe she was ready for something else, like love, and clit orgasms.

* Ladies, it might sound crazy, but people took Freud’s opinion really seriously — especially elite, well-educated women who had the most access to Freud and his ideas.

Princess Marie Bonaparte is a prime example. This woman, the great-grandniece of Napoleon and princess of Greece and Denmark was smart. She was worldly. And she really, really wanted to get off. Baaaaaaad.

Bonaparte met Freud in 1925 when she approached him for help with her “frigidity,” defined then as failure to have orgasms in missionary position. I guess everyone just wanted to be able to say, “Look ma, no hands!”

Unfortunately, Bonaparte, she didn’t just lie down on Freud’s famous velvet couch and talk about how sexually frustrated she was. She took matters into her own hands (get it?), first by doing a study on 243 women and measuring how often they orgasmed. Then she compared that with the distance between their clitoris and their vaginal opening. She found that women like her, whose clits were more than 2.5 centimeters away from their vulva, had a hard time coming from P-in-V sex alone.

With her head fill of Freudian opinions (read: lies) Bonaparte was determined to fix her faulty vagina. Unlike most women, she had the means to do so by undergoing a gruesome, ill-fated surgery.

She had a surgeon named Josef Halban surgically move her clitoris closer to her vagina. You read that right. Tragically, but predictably, it didn’t work. In sheer desperation, she even repeated the insane operation. Can someone please pass the Zoloft and the Kleenex box?

Flash forward to 2016, and we know that 75% of women need clitoral stimulation to come. So basically Freud’s early century mansplaining made three-quarters of women believe that they were fucked up.

This story just amazes me and leads me to ask, how many other lies have women internalized over the last 100 years? Lies based on the seductive, destructive, oppressive mistruth that whispers in our ears: There is something wrong with you.

The idea that every woman needs to be model-skinny, as hairless as Mr. Biggelsworth, as barbie-doll white and blond as Heidi Montag to be sexy … are just as damaging, pervasive and wrong as Freud’s stupid orgasm theory.

And by the way, Freud, when you famously said you couldn’t figure out what women wanted, maybe you should spent a little more time letting them rub on that couch of yours, a little less time making them lie face up. Capisce?

Read about Dorothy’s amazing relationship with her husband, who is her BDSM “top,” and what it’s like to be 70 and still sexual, in our next post.

Minnie operates in a different way than a lot of the women I’ve interviewed so far: she is not driven by sex or the desire to have sex appeal. In fact, sex is mostly an inconvenience to her. It’s the elephant in the room, thing that everyone else seems to be obsessed with. She can’t really wrap her head around it.

Minnie identifies as demisexual, which means someone who doesn’t want to have sex except with people they share a very deep emotional bond with.

“People have asked me, ‘Oh come on, but what about, like, Matt Damon, or some other movie star? Don’t you think they’re hot?’ And I’m like, ‘Objectively, I think they’re handsome but it doesn’t make me want to sleep with them. At all.’”

Minnie’s only really wanted to have sex with one man, someone who she was in love with but never officially dated. And aside from me and the people at the ACE (asexual) meetup group where I met her, she’s only told 3 people that she identifies as asexual or demisexual.

The thing that struck me about Minnie was this:
Minnie’s a no-nonsense person. She doesn’t like to play games and she thinks in this very linear way.
“I don’t understand girls,” she told me. “They’re always asking, ‘Does this make me look fat?’ I’m like, ‘Do you really want me to answer that?’”

So Minnie is more drawn to friendships with men.
But friendships between men and women can get really complicated by sexual attraction. Sometimes, someone decides they want more. For Minnie, sexual attraction is, at best, a bother. At worst, it feels like this wild, invisible force — impossible to control and almost as hard to understand. Because she almost never feels sexual desire.

You might understand this if you’ve ever had a best friend confess that they’re attracted to you. If you don’t feel the same way, it creates this chasm between what you want and what they want. Maybe you even wish you were attracted to them (you love them, it would make everything so easy, they make so much sense, you love spending time with them, etc.), but you just can’t get there. You don’t feel it. That’s how Minnie feels all the time.

Here’s the rub, though, Minnie still craves love, company and understanding, just like we all do. But it can be hard to parse those things out and separate them from sex when it comes to a dating relationship.

It became apparent to me though the course of our interview that not experiencing sexual desire can create as many difficulties as having a super high sex drive can. Sexuality is usually taken for granted (if you need proof, look at the magazine rack next time you’re standing in line to buy groceries). And that makes life complicated for people like Minnie.

It can take Minnie years to feel connected enough to a person that she wants to have sex.

“I have friends who say, ‘We went on a date, and we clicked. And now, I’m so attracted to them.’ I just don’t understand how you get there. I just feel like you just don’t really know that person at all after one or two dates.”

“A lot of people go to bed with someone after they’ve been dating for a month, three max. That speed is just way too fast for me. And a lot of people aren’t willing to wait around.”

Minnie has dated a few people, but in almost all cases, her partners (all male) have wanted to have sex more often than she does. it’s been even harder to explain because no one talks about demisexuality. In fact, she only learned the term a couple of years ago.

I wanted to know whether sex was fun for Minnie. Like, take the element of emotions and attraction out for a minute. Did any part of it feel good?

“I don’t need to masturbate,” she told me. “It bores me. It’s like asking someone who’s not a sports fan if they want to have a long conversation about the Giants.”

“I’ve had orgasms. It really does feel like a sneeze.”

Me: Was it a pleasurable sneeze for you?

“If you don’t have it, then it just feels like the sneeze you almost had. Like, now my nose is itching…” she said.

Aside from being Demisexual, Minnie also believes she’s somewhere on the autism spectrum. It’s often hard for her to understand the interactions she has with people, or figure out whether someone is flirting with her. So there’s often the element of uncertainty when she meets a new friend, compounded by the stress that they might want something more from her, something she doesn’t want to give them.

Without the lure of desire and the promise of pleasure, the idea of sex became more like a burden, something fraught with danger — physical and emotional. Minnie told me that she didn’t have a lot of friends growing up. So on the days when she didn’t have marching band practice, she’d often come home from school and spend hours poring over the day’s newspaper. Back then, the AIDS crisis was in full swing. No one really knew what was making so many people so sick. She read about it every day. And it scared the hell out of her.

So Minnie has experienced a lot of mismatched desires in her relationships when it comes to sex.
She dated one guy who was polyamorous for a while. He had other lovers. That worked well, in a way, because it took some of the pressure off of Minnie to have sex. But on the other hand, the guy still wanted to have sex twice a week, which was way more than she wanted to do.

But there was one person who she did want to have sex with. It was a man she worked with. She’d known him for four or five years before they really started becoming friends. I’ll call him by his initial, “T,” at Minnie’s request.

Because she’s more of a loner, Minnie doesn’t have a ton of close friends. This guy became someone who she could trust for nonjudgmental support.
“I called him once when I was on a work trip in D.C. It was the first one I’d ever been on. It was my first day and I was walking around and I got totally lost and I was tired and starving. I had no idea where to go. So I called him up on the phone. He just told me, ‘Calm down, you’re ok! Just go up to the nearest person and ask them were you can find a good meal.’
I did what T said. The nearest person was this nice, older, doorman. He pointed me to a restaurant across the street and told me to order the mussels. They were delicious. Then I was totally fine.”

“T was someone who I could call, you know? He wouldn’t tell me I was stupid or judge. He’d just listen and try to help.”

After years of knowing one another and months of becoming closer and closer friends, Minnie and T were texting every day and having dinner together at least once a week. Finally, Minnie kissed T. A while after that, they also slept together. For the first time, she actually wanted to have sex.
But by the time that happened, T also had a girlfriend. The girlfriend, suspecting something was going on, moved in and demanded that T stop talking to Minnie entirely.

They tried to meet up and be friends, but they would end up having sex and eventually, he told her he couldn’t see her anymore.

“I think it’s hard for him to see me and not have the urge to sleep with me. But now that I don’t see him anymore, I wonder, were we even friends? I’d like to think so, but I don’t know. I wish I could meet someone who just wanted to be friends until we got to know each other better,” she said.

“My aunt and my uncle who grew up in Hong Kong were friends for 7 years before they kissed or anything,” she said. “Not that things were all that great back in that era, but, a really long courtship sounds nice to me.”

Thanks, Minnie.<3

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Ricki used to work with kids who have Autism, but after she got injured a year and a half ago she decided to take a break to focus on getting well. She found a houseboy (as I covered in the last post), dialed back her work schedule, and discovered another way to make money: cuddling. She knew a friend who’d worked at a San Francisco cuddling salon and decided to give it a try.

She charges $80 hourly and makes $65-$70 after giving a cut to the website where she lists her services.

“It’s my best form of money making at the moment — it’s four times what I normally get paid hourly,” she told me.

When Ricki told me about professional cuddling, it was sort of like when she told me about having a houseboy. It sounded a little too good to be true. Do people really just keep their clothes on?
She insisted they do.

“They come in and lay on my bed and we just cuddle. Sometimes we have music on sometimes we don’t. Sometimes we talk, sometimes we don’t. It’s whatever they want.Sometimes I have to redirect hands and sometimes you can tell that there’s a sexual tension. In that case, I try to kind of shift it in another direction.”

I’m not clear whether cuddling falls under the umbrella of sex work. For me, it feels more like compassion work. It reminded me of the work that Amma, known as the hugging goddess, does. Ricki agreed.

“It involves holding a lot of space for someone else and providing a safe and certain type of intimacy,” Ricki said. “It has taken me a while to learn how to set boundaries and do self care, because I am a very empathetic person and I can absorb other people’s stuff. When they’re stressed, for example, I can take on that stress.”

I think this is a universal struggle for all empathic people. Except Ricki literally brings these clients into her bedroom.

Recently, she’s been able to figure out ways to remain empathic while setting boundaries that keep her sheltered from absorbing other people’s energies so much.

“These days I’m present (during the session) but then they leave and I’m done. I have to stop thinking about them, or whatever energy they put in or whatever they talked about — I’m done. At that point, I’ve provided my service and hopefully it’s provided some amount of relief or comfort to them.”

“I try not to overbook myself. I drink a lot of hot tea now and take time alone.The other thing is that all of this is happening in my bedroom and in my home and in my space. So I change my sheets a lot— not because they’re dirty. But removing them and cleaning them and bringing them back feels good.”

I checked pro cuddling out online.

One of the first links I found was on the website The Snuggle Buddies, one of the largest and most successful sites.
Some observations. 90% of the cuddleworkers (like what I did there?) on the site were women. Not that surprising, but worth a mention. Also, women posted photos with their bios. I guess, yeah, this might be obvious, you want to see who you’re signing up to cuddle. But also, if it’s non-sexual touch, how much should looks matter? The photos, granted, were not overtly sexual. They looked more like tame Facebook profile photos.

Ladies, hold on to your aprons, you may never want to do housework again after you read this.

Aside from being a lovely, thoughtful, self-possessed person, who was a pleasure to interview, Ricki opened my eyes to something I knew nothing about: Houseboys.

It all started when Ricki had an accident in 2014. She hurt her spine, had trouble walking and doing things around the house. She couldn’t sweep or cook herself dinner. She was getting terrible headaches. Something had to give.

Ricki is comfortable in the Kink community, so although she usually considered herself a “submissive,” she decided to post adds on Craigslist and the BDSM social networking site, Fetlife with an open call for a houseboy who would clean her apartment, carry her basket in the grocery store and take a few slaps on the face when he didn’t do it right.

She got responses, lots of them, or so she told me.

I kind of didn’t believe her. So I decided to do a small experiment.
I was like, how many dudes would really want to do this? Maybe my incredulity had to do with the fact that I hate doing house chores.

So just to see, I posted an add on Craigslist.

Here’s what I got in less than ONE HOUR.

Then, just for fun, I changed the post to say that sex acts WOULD NOT play any part in the relationship.

I still got some responses, in some cases, because the dudes didn’t really believe the non-sexual thing. In other cases, it seemed like they were willing to engage in something that was purely psychologically arousing for them. Here are a couple of my favorites.

Back to Ricki.
She told me all about what she does with her houseboys and how the relationship works. Despite being the one who gets served and doted on, Ricki puts a lot of energy and work into choosing the right person, grooming them, and following through with reinforcement or punishment — depending on what the occasion calls for.

But back to how all this starts. After she gets the initial responses on Craigslist, Ricki has her houseboy applicants fill out a four-page questionnaire. That’s right, a four-page questionnaire. That’s the reason I will continue to muddle through with my own housework, despite doing a completely insufficient job at it, and why Ricki works to cultivate long-term relationships with her houseboys: It’s a lot of work to create a working relationship, one where both people are fulfilled. And Ricki takes that seriously.

“My houseboys usually wash my laundry, change my bedding, take out my trash, wash my dishes, clean the entire apartment. Sometimes I take them out with me to go run errands and they hold my hand basket and push the cart. I point at something and it’s retrieved. They take in all of my groceries and unload them.”

“They’re like a partner that does everything without ever arguing.”

Before she ever invites a would-be houseboy over, they get together for coffee to see if they mesh and go over the questionnaire.

If it goes well, she’ll have them over, tell them what she wants done and how, then relax or do her homework while they go at it.

Ricki said that despite what some people think, the houseboy-mistress relationship isn’t about a Freudian son/mommy fetish. It’s more of a mentor – mentee thing.

“I want to make my submissive into the best version of themselves that they can be.”

“I think some of these people actually just want someone who will make them be accountable. So they also get more things they want out of their life. I can be a built-in accountability person. And they want to please me. So, for example, if I know that they think they should be going to the gym because it helps with their depression, but they haven’t been, I’ll make that one of their tasks during the time I don’t see them.

After the houseboy is finished with the chores at her house, Ricki will usually cuddle with them and talk. And then, Ricki might have them pleasure her sexually, if she’s feeling it.

That’s right, ladies, the houseboy’s altruistic duties need not end at the bedroom door.

Ricki said those interactions have been a great learning experience that has actually helped her enjoy sex more, whoever she’s having it with.

“I’ve gotten a lot better at asking for things and telling people how to touch me.” she said.

The houseboy really wants to do what Ricki asks, and she isn’t expected to do anything in return. So it’s helped her get clear on what she wants and figure out exactly how to articulate it.

“I think initially I felt a lot of guilt and shame around receiving (before). But that has gotten a lot easier.”

And friends, that can only be good news. I feel like if more women were able to dive into truly receiving pleasure, we could end wars, save the whales and everything in between.
But hey, that’s just me.

Also, stay tuned, folks, because there will be a Part II interview where Ricki talks to me about being a professional cuddler.

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Hey readers,
Up to this point you’ve probably seen interviews with a lot of sex positive, polyamorous, queer folks on this site. This story is totally different. And I’m really happy about that, because I want all voices to have a space here. If you were raised Christian, this might sound familiar to you. As someone who was raised Catholic and is not anymore, I found it fascinating.

Sara is a bawdy, unapologetic woman — the kind who seems incredibly honest because she doesn’t even consider another option and who doesn’t take herself too seriously. She can’t. She teaches health to high school kids. She’s also Christian.

After a wild and saturnalian sex life in her early 20s, she’s limited herself to sleeping with two men in the last decade, despite her urges to sleep with many many more.

“Am I still horny all the time? Hell yes,” she told me.

Lucky for me, Sara isn’t shy about talking about sex. She does it as part of her job.
“I’ve been asked everything under the sun (in Sex Ed). Sometimes I have to tell the girls, “No, honey, it’s not true that all girls ‘do’ anal.’”

Sara was raised in a very small, very conservative Christian town, where she felt pretty alone. She just never really found her people there.

“People were always having barn parties. But I hate country music and I hate beer. So I was just like, ‘What am I doing here?’”

Sara said she has always been sexual. She couldn’t remember the first time she masturbated or had an orgasm, but the former was probably some time around 12 or 13. No one talked to her about masturbation, she just figured it out.

“I’ve always been horny. I remember listening to Janet Jackson singing “If I was your girl” in middle school. Oh boy,” she said.

She dated boys in high school, but it wasn’t until age 19 that Sara had sex for the first time. It wasn’t great. She didn’t feel ready. Back then, she says, she was pretty insecure. Part of it came from growing up in a very “white” town where she felt like men didn’t value her thick frame. She’s also always been attracted to black men. So when she got to college, she began to meet more black and Latino men who liked her body and who she found hot.

35 men in 2 years
Things took a sharp left turn when Sara went to grad school. She was in a sports training program and surrounded by a lot of hot people with nice bodies. She was also suffering low self esteem and depression. Sex was a way to feel beautiful, to feel loved and cared for. She and her friends would go out clubbing five nights a week. More than half the time, Sara would take someone home. She didn’t want to date these guys. She just wanted to fuck.

“I began to use men for sex the way that men use women for sex. I remember this one guy who got so offended when he found out that we weren’t dating. I had given him no indication that we were, he just assumed it because we had been having sex. And I was like, ‘No, man, you’re just my backup. You’re the one I call when other people fall through.’”

But some of the encounters were memorable, like the first guy who Sara said, “totally blew me away.”

“This guy was an olympic sprinter. I mean, he had legs like Hercules. He picked me up off of the floor and took me to the bedroom (pregnant pause) and then he went for hours. He made sure I had more than one (orgasm) before he came.”

“That was fun,” Sara said. Damn fun. Except, because of her beliefs, Sara always felt conflicted about having sex with people she wasn’t married to.

Sidenote: What I love about Sara is that even though she said it was wrong to sleep with all those men, I didn’t get the feeling that she was judging herself. That was really refreshing. I’m sure it’s that same lack of judgement that allows her to be a trusted confidant for the teens she teaches and the young girls who are in her church youth group.

Some girls come to her after they’ve “given into temptation” and had sex with their boyfriends.

“I tell them. Hey. It’s ok. This isn’t the end of the world. Everyone else is like, ‘You’re a sinner. Get out of here.’”

Hard pause on the sex
Then when she was 26, Sara was at an Easter Sunday church service when something hit her. She wanted to change her life, she decided, and start living by what she believed in. That included waiting to have sex until she was married — or at least trying.

What followed was a long period of abstinence. It was hard, Sara said, and emphasized that she has no self control in general, which I thought was a bit of a harsh overstatement.
But it was also very healing. Before, she said, she felt like she was “pouring herself out,” in some essential way, and giving up something important by banging anyone who gave her a second glance.

I challenged her on that a little, because I feel like that wording makes it sound like women can be “used up” or only have a certain amount of sexual energy to expend in their life.

But I also heard what Sara was saying. We all do only have a certain amount of physical, emotional and psychological energy, just like we only have so much time in the day.

She also said that using her faith as a reason to abstain helped her look for character in men.
“Before I was looking for the guy I wanted to lay that night. Now I look for the guy I want to lay over and over again,” she told me.

Sidenote: I’d like to interject that I’ve also seen people who sleep with many people do the same thing. You can be sex positive, having a lot of short-term sexual relationships and still be on the lookout for character in a long-term partner. I think the key thing is that Sara’s faith and her community gave her the strength to set some healthy boundaries for herself, boundaries that made her life happier in a lot of ways. On her own, she wasn’t really setting those boundaries for herself.

She’s had sex with two long term boyfriends over the last ten years and said it’s been more emotionally and spiritually satisfying than the sex she was having before. She’s been having sex with people she really loves now.

Here’s the rub though, Sara told me that she also believes it’s wrong for her to sleep with her current boyfriend, even though she still does it and doesn’t really believe she’ll stop. People can judge her, she said. But she isn’t perfect and neither are they.

“Sex is not a part of my ideal dating relationship. Because I believe in a God who tells us to save ourselves for marriage,” she said. “… Even though finding people online to date when you’re not givin’ it up is tough.”

Then she used the duct tape analogy.

“If the purpose is to bind two people together, it stands to reason that you’re going to be more bonded to the first person you have sex with,” Sara started telling me. “Like me, I’m always going to be comparing the man I eventually marry to all the other people I’ve had sex with. Sex is like duct tape. It’s really sticky the first time you stick it on to someone else. But then as you keep pulling it off and sticking it back on to new people, it gets less sticky. At this point, sex doesn’t bind people like me in the same way because I’ve had so much of it. My duct tape doesn’t really work anymore. It won’t bind me to my future husband the same way it bonded my sisters, who were virgins when they got married, to their husbands.”

Here it got very Adam and Eve for me. I was like, wait, so you’re saying that knowledge is a bad thing? How can that be true? Knowledge is power!

Here’s what Sara said to me, which I thought was interesting.
“Imagine that you had only ever had Hershey’s chocolate in your whole life. And you’re like, ‘This is the best chocolate ever’ and then you go to France and you taste the chocolate there and now you’re like, ‘Wow, Hershey’s is shit!’ Well, that did nothing for your enjoyment of chocolate.”

In other words. If you get married and the sex is so-so, but you never know anything better, it might seem great to you. Knowing you can have better sex won’t make you happier if you are firmly committed and intend to stay with the person you married.

It reminds me of the way the Buddhists talk about desire as the root of suffering. That religion leads people on a path where they can relinquish desire. To follow this teaching, it seemed like you avoid desire by not knowing what you’re missing.

To illustrate more, Sara told me about her ex boyfriend. He had a small penis.

“I would never have known that if I had not slept with so many other people. And because of that, I was expecting him to be like some of the other guys I’d slept with,” she said. “He still got me off — really well. It was just in a different way. But I was comparing so he seemed like ‘less’ to me.”

I might counter that if you have sex before marriage, and sex is really important to you, you could find someone who meets your needs, including the kind of sex you want. You’ll likely make the decision based at least in part on physical attraction, which boils down to sexual attraction, anyway.

But the Christian teachings that Sara believes in say, find your partner first based on all the other criteria like character, then have sex as a great add-on. And without agreeing, I respect that.

“I feel like in this culture we live such public lives. It feels like it makes sex more special to keep it for just one person. I believe that sexuality is something with a lot of value.”

I asked Sara to explain what she meant that it had a lot of “value.”

“Like, I have this very close friend,” she said. “We’ve been close for years but she just told me something really important and personal about her past last week. So I’d say she’s someone who places a high value on sharing her past, she only shares with people she really trusts. So we also believe in placing a high value on sharing sex.”

The takeaway
The takeaway for me was that Sara’s faith helps her make healthy boundaries for herself. It’s also helped her reaffirm her innate value. Also, Sara doesn’t judge, which is one of the most important, often overlooked teachings of Jesus, in my opinion. I got the feeling that she genuinely wants other people to be happy, to enjoy life, to enjoy sex. And she wants the same for herself. And she’s honest. Thanks, Sara.

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Name: Heidi
Age: 37
From: San Diego but lived in Norway for six years and Spain for two years
Job: Runs a cultural exchange program for Americans in 25 countries

Heidi grew up near the beach in San Diego. She was a cute, fun girl with a lot of friends. Like a lot of girls, though, she felt insecurite when she compared herself with the super hot, super “popular” girls who always had a boyfriend on their arm.

“San Diego is very judgey, very based on looks, and all the hot guys are pro surfers or pro skaters. It’s a very image-based scene,” she said.

What is a “late bloomer” anyway?
Heidi told me that because she didn’t have a boyfriend in high school, she felt like “kind of a late bloomer” sexually. I was expecting her to say that she hadn’t had sex until she was in her 20s or something. But then she continued to tell me about having sex at 17 with a friend of a friend.

Sidenote: I want to reiterate something I’ve said before, how it keeps wowing me how much our ideas about what’s “normal” and what we “should” be like are formed by the wildly varied, subjective, man and woman-made environments we all grow up in. I know this seems obvious, right?! And I think many of us are aware of it. But despite that, everyone seems to unconsciously absorb some of the norms they grew up with in a way that makes them feel more true than they really are.

Thank god, if you’re exposed to a lot of different people, you might find out that what you thought made you weird isn’t weird at all. Because everyone has at least one thing about them that they assume is not normal.

But back to Heidi.

Love abroad
During college, Heidi studied abroad in Denmark. While she was there, she fell in love with a “really good, really handsome Norwegian man.” After the program ended, she moved to Norway to be with him. She was in love and tried to mold herself to fit into his life and his culture.

Domesticated with Prince Charming
She was living abroad and learning new things, both really important to her, but as the weeks wore on, she was also getting claustrophobic in the suburbs.

“I was, like, such a good girl when I moved to Norway. I didn’t smoke weed, I didn’t do anything. Norweigans follow the rules very strictly. And then I kind of felt like I lost a bit of myself because I tried to conform to something that I wasn’t, really,” she told me.

Heidi was playing the part of the “good girl.” But at her core she certainly wasn’t only that.

“I thought, ‘Oh my god, I’m going to live in the suburbs of Norway and have five babies.’”

The orgy with Vittorio the Italian drug dealer
During the interview, for instance, Heidi told me about several sexual experiences she had had around the time she dated the Norwegian guy. In one case, she was partying with her girlfriends in Oslo. Everyone took “Molly” (aka MDMA) and went out. Somehow they ended up at an Italian drug dealer’s house (his name was Vittorio) and started having an impromptu orgy.

“Everyone just started having sex everywhere and touching everyone and getting in there,” she said. “It was kind of awkward because two of my best friends were there.”

Another time, she was in a hostel in Botswana with her Norwegian boyfriend. After he went to sleep, she ended up having a threesome with a guy and a girl.

That is to say, Heidi was 24 and probably not ready to settle down just yet.

“From the white knight to the bad boy”
What happened next is what usually happens: the dark horse showed up. In this case, he was the hot latino chef at the Spanish tapas restaurant where Heidi worked.

“I went to this party and he was smoking the fattest joint I’d ever seen, and I was like, ‘This guy is badass,’” Heidi told me.

Even though the Norweigan was a good boyfriend, Heidi needed something new. She broke up up with him and started dating Spanish chef, Alex.

“I went from the white knight to the bad boy. He was so unlike me but I was so attracted to him. It was a whole new world.”

They had great chemistry, but the relationship had some crazy highs and lows. There were drugs. A lot of drugs.

Heidi and Alex moved to Spain for a while, where Heidi (who had studied journalism) worked at a press agency.

But then Alex lost his job and things began to fall apart, fast.

“Stuff is blowing up, let’s get married”

“We ended up doing tons of coke and spent tons of money. It was really unhealthy. But at that point, I needed (work visa) papers and I was like, ‘Hey, we need to get married.’”

Heidi said that when she looks back, it’s obvious getting married wasn’t the best thing to do.

“But at the time I needed work visa papers. I was very weak and I didn’t want to break up and I didn’t want to go home … I was trying to fix the relationship that was already broken.”

Heidi and Alex ended up moving back to Norway. She waited for papers while the snow piled high outside. Meanwhile their relationship got more abusive and strained. Heidi was rail thin. Cocaine and cigarettes had replaced food.

Then one night, in the thick of an ugly fight, Heidi decided to make a different choice.

A one-way ticket home

“I remember the night I bought a one-way ticked home. Alex was screaming at me and I just pressed ‘purchase.’ And then it was done.”

“I was kind of a mess after the break up. I felt pretty defeated. I quit my two jobs and said goodbye to all of my friends.”

Heidi let people know on Facebook that she was moving back to San Francisco.

“Within an hour one of my best friends from childhood told me that she had a room for me in San Francisco for $600. I took it immediately. It’s still the apartment I live in today.”

Once she moved back, Heidi had to start over with everything. It had been years since she’d lived in the US and she had to start putting down roots again. But her closest friends helped her find herself again by getting her an interview for a travel coordinating job, taking her out, introducing her to new people and encouraging her to start writing her own blog. She kicked the cocaine habit too.

Heidi didn’t date anyone for almost a year after she moved back. Then she said, she started casually dating and sleeping with a lot of people.

Sometimes she even ignored her therapist’s warning and Skyped with Alex. At one point in a moment of weakness, she invited him to move to San Francisco.

“Thank God that didn’t happen,” she told me.

She eventually payed $2,000 to finalize their divorce.

Seeing rainbows
Then one night, Heidi went out to a concert with her sister’s friend. Heidi had met her a few times before and they got along great, but she never thought it wold be anything more. But after the concert, they ended up hooking up with each other and realizing that along with loving the same music and having a lot of fun, they had really great chemistry as lovers.

But neither of them was ready to have a girlfriend. And while Heidi had always been bisexual, she’d never dated a woman. So the pair spent “a wild year of being best friends and lovers” until they realized they just needed to date exclusively.

They’ve been together 4 years now.

Before, she said, the people she was in relationships with were so different from her. She seemed to seek that out, but it was so extreme. With her girlfriend she says, there is way more compatibility.

It seemed like she’d found a way to be herself and be with someone she loves deeply — a person who, by the way, apparently makes her “see rainbows” when they have sex. (How’s that for a double entendre? )

“Now I feel pretty comfortable just being myself and I think my partner loves me for who I am,” she said.

She said that although her friends and family are very supportive, it was a little weird when she first came out.

“Like, trying to tell your parents at 32 that you’re dating a woman is a little weird. I just said I was bisexual to ease them into it. My mom was always trying to ask me, “Are you lesbian or bisexual?’ And I was just like, ‘I don’t really know, mom, it’s kind of whatever you want it to be. For me it just depends on the person.'”

Plus, some people think they’re pretty open minded, but aren’t.

“I remember some people being like, ‘I’m totally cool with the gays,’ and then they were not … A lot of my guy friends got really territorial too, asking my girlfriend, ‘Hey, why you stealing our girl?'”

It’s now been four years since she started dating her girlfriend now and Heidi said that pretty much everyone close to her knows, loves and accepts her for who she is.

When Heidi looks back, she’s so happy that she was able to pull herself out of the those past relationships when she did, even if it wasn’t smooth or graceful all the time.

“Back then, when I broke up with Alex, it did feel like I had failed in some way. But now I am so so happy that I did. My life seems so much fuller and complete now,” she said.

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When we left the last episode on Jessica, she had just started to transition.Here, Jessica tells me how Estrogen changed her orgasms, the various surgeries she’s had to achieve her physical transformation into a woman and things no one tells you about vagina surgery.

FYI: This post includes some Q-and-A formatting.

Me:Tell me what it felt like to start taking Estrogen as part of hormone replacement therapy.

I’ve heard stories of what it’s like to take Testosterone (from women transitioning to men) and it sounded crazy: insane sex drives that made them want to bang everyone in sight, steroid-like rages and superhuman muscle growth.

Jessica:“One analogy I like to use is that I felt like I was Dorothy waking up in Oz. I’d been in black and white land for a really long time. Then, with Estrogen, I was seeing life in living color for the first time ever.

I finally felt like my emotions had this crystal clarity, like they had a vocabulary to them, and like I could understand and process them without being so caught up in them. I could take a step back and look at them and be like ‘Oh! That’s what’s happening!’ rather than being confused and sort of flailing around and getting angsty and emo.

Prior to that, I knew I was an emotional being, that I was sensitive, but it was so much harder to do that. I just felt like things made so much more sense.”

But, of course, having permission to express emotions involves cultural pressures, not just hormones. Jessica also felt she had more permission to express herself as a woman than she’d had as a man.

“It’s just a horrible reality of patriarchy that men aren’t allowed to show emotions.”

Physically, she said, the lines of her face and body began to round out. Fat started accumulating around her hips. Breasts started to emerge on her chest. She also noticed her sense of smell had gotten stronger. She could smell men.

But there was another emotional component, too.

“I also felt that I was undoing a lot of what I saw as damage that was done to my body because of the first puberty that I went through — the first puberty that I didn’t choose.”

New Vocal Cords, Breasts, and Vagina
After she started doing hormone replacement therapy, Jessica took a plane ride all the way to South Korea, where a doctor was pioneering a unique type of vocal chord surgery and took her as a patient. Jessica’s original voice was a deep baritone that sounded very “manly.”

In order to get her voice to come out at a higher pitch, the doctor fused one side of her vocal cords together so that air passing through her larynx would produce a higher-pitch sound.

Jessica’s voice is on the deeper end of women’s voices, but it’s definitely a female sound. She came home very happy with the surgery.

So now Jessica had a woman’s voice, budding breasts and womanly curves. There were only a couple more steps to complete her transformation.

In a moment of intense ambition, Jessica decided to get a breast augmentation surgery and a vaginoplasty in a single operation near her home in the East Bay Area, CA. She now stresses that she does NOT recommend doing both surgeries at once.

“I woke up in the recovery room in a world of pain, unable to move,” she said. “I really underestimated how much the recovery from breast augmentation takes out of you.”

Luckily, she said, it wasn’t as painful as it could have been on her wallet. She paid for the boob job herself. But her vaginoplasty was covered by her insurance as mandated by California law (because a doctor deemed it medically necessary).

Jessica had an advantage during her recovery. Her partner, who was also born male, went through the surgery before her. But there were things that happened (for both of them) that no doctor had told them about (even though they damn well should have).

“There are are going to be parts of you that are going to melt off,” Jessica told me.

Here’s where I asked Jess to elaborate about a whole bunch of things about her new vagina, how it healed and how it works:

Me: Can you tell me more about your pussy “melting off?” That sounds horrifying:

Jessica: “It is really scary. But it’s also perfectly normal and most people recover from that completely as if nothing has happened.”

“Basically the furniture down there gets rearranged during the surgery. One of the many things I learned along this journey is that male genitalia and female genitalia aren’t that different. They’re arranged differently, but the individual parts are really similar.

So Vaginoplasty consists of a repositioning and folding of all these tissues using the existing tissues. When that’s done, some of the tissues might not get as much blood flow as they did before, so they get starved of nutrients and oxygen.

That’s when the surface tissue tends to die off — which is as gross as it sounds. It is really really awful. Everyone knows that their pussy is going to look like Frankenpussy after surgery. It’s red, there’s stitches and it’s swollen, you can see the stitch lines. You expect that. What you don’t expect is this yellow-y, clumpy, almost mucus-y, looks-like-someone-sneezed-on-your-pussy kind of residue.

So you might have a chunk of your inner labia just die off, just fall off, and it’ll just grow right back. It’s hard to believe because when you lose a limb or a toe it doesn’t grow back. But it turns out that your pussy does. It’s strange.

And it’s gross and it’s funky and it’s awful and you think, ‘Oh my god, What is happening? My pussy is melting. I’m dying.’ But it turns out that it is perfectly normal.

It’s something doctors should tell patients beforehand. Because you’re already dealing with so many changes, working with so many geographic changes on your body. Your clitoris, which used to be the head of your penis, is positioned in a completely different way.”

ME: Do you ever get a phantom limb feeling where your penis used to be?

Jessica: “There were times early on when I felt like I could feel my penis. I figured out what was going on though. Basically, my clit was telling me that it was still the head of my penis, that the most sensitve part of it was still there. It took a lot of adjusting and it was pretty weird at first.

Me: How does your pussy look? Does it look like a cis-gendered woman’s pussy?

Jessica: “I’ve been told by cisgender females, lesbians and bisexuals that it looks just like a pussy should. And those are obviously people who have had a good look — a face-full of pussy as it were. So yeah. They’ve told me it’s pretty and that the surgeon did a great job.”

Me: Let’s talk functionality … Does your new pussy function like a regular one? Can you have clitoral and G-spot orgasms? (This to me, was the most interesting question of all. For some reason, I’d been under the impression that vaginoplasty pussies weren’t completely functional. Turns out I was COMPLETELY wrong, and I’m super glad that I was!)

But the part that really fascinated me was that Jessica’s orgasms changed even BEFORE she got a vagina, back when she was initially taking estrogen.

Jessica: “I do have a G-spot. In fact, I still have a prostate, even though it’s much smaller than it was because of hormone replacement therapy. But it’s still there and it can still be stimulated. It’s still very enjoyable.”

Me: What about orgasms? How is an orgasm as a woman different from an orgasm as a man?

Jessica: “Orgasms are very different. Oh my goodness. They were different even before my surgery after I started hormone replacement therapy. That’s when I started having more full-body orgasms. The sensation wasn’t just concentrated immidiately around my genitals anymore. It was more like waves of pleasure throughout my body. So that started happening with just hormones. But then, of course, the surgery changes everything.

When I still had a penis, when I climaxed, it kind of had this punchiness to it, this moment of just intense pleasure, hitting you like a truck. That male orgasm pleasure just built and built and then BOOM it just exploded like a firework.

Now my orgasms are this gradual build to this raging fire that just blazes for like 15 to 40 solid seconds where I’m climaxing and my mind is just clear of any distractions. I’m just completely in the heat of the moment, my mind is empty and I’m just experiencing pleasure and it just lasts for so much longer than it used to. Coming down takes a lot longer than it used to. But I can have multiple orgasms now. Most of the secondary orgasms are energy orgasms, where I feel waves of pleasure through my body but not the intense contraction and pleasure that I get during my initial orgasm.
I also discovered that I’m a bit of a squirter … Or, I don’t really squirt, but I gush. I drench my hands every time I masturbate. It’s kind of amazing.I didn’t think that I would get such good results from my surgery but there they are.

I definitely experience internal stimulation orgasms and they are different from the orgasms I get from clitoral stimulation. They’re deeper and they’re more intense — always gush from internal orgasms.”

Me: Wow, I’m so happy and amazed to hear this. Is this kind of experience you’ve had pretty normal? Or are you the exception?

Jessica: “Most of the trans people I’m close to have had similar experiences. They may not gush as much as I do or they may prefer clitoral stimulation over internal stimulation, but most of them agree that penetrative sensation feels really good. I think it also depends on the surgeon and when they got their surgery.

Surgery techniques now are a lot better than they used to be even 10 years ago. So some things are different for trans feminine people who had their surgery 10 years ago. Doctors have gotten to a point now where they can make a vagina that allows you to come and really gush from internal vaginal stimulation just like a cis-gendered woman does, if that’s something that you’re capable of doing. That’s a pretty common experience I’ve seen among people in my chosen family.

I knew that going into my consultation that things were really good now medically, and that was a motivation for me to get a full-sized vagina with a vaginal canal as opposed to a shallower one.
There are people who have chosen to get shallow vaginas or no vaginas at all, just a vulva. And their recovery process is much much simpler.”

Me: Is that why you decided to get a vagina with a full vaginal canal? So that you could experience penetrative sex?Jessica: “Yes, that’s why. I also wanted to be able to relate to cis-gendered women in a way that I felt would have been impossible otherwise. So, I get it now, in the sense that I’ve had to wear a pad for months. I like to think of it as making up for lost time … Had I been born with a pussy I would have gone through all these periods and instead, after the surgery, I ended up having one really long period that lasted for months and months as my vagina was bleeding during recovery. I had to wear a pad every day and I get it. The struggle is real … I have this newfound respect and empathy for my fellow sisters. I get it now.”

Me: I heard that you just had your first penis-in-vagina sex. What was that like?

Jessica: “Yes! I just had my first p-in-v sex as a vagina-haver and it was different from what I expected. It was more intense than I expected. I had gotten used to the process of dilating my vagina, which I do with a medical phallus one to two times a day, to keep the new vagina from closing up. I’ve been doing that for 9.5 months since my surgery. So having something in my vagina is a normal sensation for me because I experience it every day.

But having a person inside my vagina was a relatively new experience for me. I’ve had fingers but I’ve never had a penis. It was a little overwhelming, but it was pleasant and fun and I would totally do it again. The person I had sex with was a preoperative trans woman. She still had her penis. And she’s just a sweetheart. And I’m so happy that my first experience was with her because she’s just super sweet and super attentive and very feminine and I wouldn’t have had it any other way, being that I’m a lesbian. It was pretty cool.”

Me: Do you tell new partners that you were assigned male at birth? In other words, do you “come out” as a trans woman before you sleep with someone new?

Jessica: “That was a conversation that I felt I needed to have before surgery, more so than now. But I feel fortunate because I’m a queer woman who’s mostly interested in women and I’ve never had an experience where people are grossed out or shocked and stunned. I’ve never come out to anyone and seen it change their opinion of me or their decision to be intimate with me.

But I can imagine that if I were to start dating cis-genderd, heterosexual men, it would be a much more daunting and scary prospect. Many transgender women suffer violence and sexual assault when they reveal to their prospective partners that they were assigned male at birth.

There’s a lot of transphobia out there and it’s a scary conversation for many trans women who are interested in men. Fortunately I have not had to deal with that in as scary a way. And I am not at all interested in cisgendered, straight men. I have been attracted to cisgendered queer men. There is something about queer men that is much more safe. Especially those that are in the greater LGBT community.
I feel like the prospect of telling a bisexual man that I was assigned male at birth sounds much less scary than telling someone who’s been cis and straight their entire life.”

Me Again

Jessica freakin’ stole my heart. I can’t help but feel like trans people like her have a very special appreciation for what it means to be a woman. All I can say is, it’s damn good to have you. I’m hoping (and betting) that you and your vagina are going to have many years of happiness ahead.

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Sera grew up in Ethiopia. The example of womanhood she saw growing up prioritized the home and taking care of husband and children. But Sera knew early on that she didn’t want her life to look like that and vowed that she would do things differently.

Now 24, Sera has become strong and independent in a lot of ways her mother wasn’t able to. Sera isn’t married to her boyfriend, she said, because she doesn’t believe in marriage.

She watched her mother beg for permission to leave the house
“Staying at home, waiting for the husband, cleaning for the husband… I like to go places myself and to work outside the house. The worst moments when I was a girl were when I saw my mother ask my father for an allowance or for permission to go somewhere. I hated that. My mom waited until she was married to have sex with my dad. He’s probably the only person she’s ever had sex with. She isn’t happy. I don’t want to be like that.”

But there are still challenges. Right now, Sera feels stuck in a relationship that isn’t fulfilling, but that she stays in.

I met Sera when I walked (notebook in hand) into an Ethiopian hair braiding salon in the Temescal neighborhood of Oakland and encountered some inquisitively furrowed brows and squinting eyes. Sera had just arrived with her chubby-cheeked, 1-year-old son in tow. When I asked the stylists and customers if anyone was willing to let me interview them about some really personal stuff, Sera said, “Sure, you can interview me,” without batting an eye.

While the stylist ruthlessly tamed her hair into neat rows that swirled around her scalp, Sera told me about the man in her life. He’s the only man she’s ever had sex with. They met when she was 18. It was summer in Oakland and she was lounging at the public pool with a friend. She’d never really dated anyone before.

He saw her and wrote his phone number down on a piece of paper. He gave it to a little kid, who couriered it over to her. Sera was flattered.

“I was very innocent back then,” she told me.

They went on a simple date at a nearby park a couple days later and decided to make love almost immediately. Sera was beyond ready to lose her virginity, despite warnings from her religious, traditional mother not to sleep with anyone before she was married.

“It wasn’t very romantic. On the way home from the park I was just like, ‘Let’s do this.’”

Caught up in the thrill of new love and novel experiences, Sera felt fulfilled. She had a newfound freedom with him by her side and a new reason to have some new adventures.

“I never used to go out and do things before him, so when we first went out, it was just so fun. He took me everywhere. Everything was new. Now it’s not fun anymore.”

Sera’s ideas of what she wants have changed in the last six years. But she’s stayed with him, despite becoming ever more dissatisfied.

Cheating f**** with your head
She’s been going through an especially hard few months after she found out that he was cheating on her last November and had been since her son was three months old.

It happened when she called his cellphone one day and heard a woman pick up the phone.

“I figure all guys cheat, but the way he did it, it just seemed like he didn’t try to protect my feelings,” she said.

“I told the woman on the other end to come over and get his stuff and move it over to her house… but she still hasn’t come,” Sera said.

Sometimes they’ll have a row and she’ll tell him to pack up his things and move out. He’s put his stuff in a bag as if he were going to leave before, but he’s never gone through with it, so they’re still living together in Oakland.

When she looks back, Sera realizes that the things she wants and needs from a man now are not the same things she was looking for six years ago. Back then she wanted someone manly and tough. Now she just wants someone who will listen to her, help out and be sensitive about how she’s feeling.

“I wasn’t looking for nothing then,” she told me. “Then it was just for fun. Now I want someone who’s supportive. Someone who’s there, who you can count on. I actually want someone who’s oversensitive. Like if it were possible to have someone who cries every day, I’d probably like that person.”

Men, if any of you just got teary eyed, email me and I’ll give you Sera’s digits.

One of the worst parts about the cheating thing is that Sera hasn’t felt comfortable having sex with her boyfriend since it happened. When we spoke, she said they’d made love twice in about three months.

That might be fine for some people, but Sera likes having sex — a lot.

“I’d probably do it all day if I could … in fact if I was single, I’d probably whore myself out just to get experience,” she said.

Sidetone: I couldn’t tell if Sera really meant that, or if she was just tempting fate, daring herself to seek out something more crazy and interesting — an extreme remedy to the extreme lack of sexual contact she was suffering from.

Sera’s been trying different things to make herself feel better after the cheating. Getting her hair braided was one of them.

“When someone cheats on you, it makes you want to change things about yourself. To build yourself back up again … I’m trying to be more girly… I’m not a ‘girly girl.’ Like wearing makeup, taking hours to get ready, not wanting to get dirty — that’s not me,” she said as she flinched and the stylist pulled a section of hair into a tight braid that clung to Sera’s scalp.
“I’m gonna have Chinese eyes when this is done,” she said.

Having children is something that Sera never sought out— even though she loves her son and seemed to be doing a great job with him.
“I never wanted to have a kid,” she said.

A kid and an affair will really ruin your sex life
Even before the cheating, she said, the birth of her son all but ruined her sex life with her boyfriend.
Before he was born, sex was an eight on a zero to ten scale.
Now it’s more like a two.

“After you have a baby, your relationship changes. You’re not there mentally,” she said. “Even though he’s there, it’s the woman in the relationship who grows up and has more of the responsibility.

He’ll still be like, ‘You can’t find a babysitter? Well, I’m still going out,’ and I won’t stop him. But at the same time, I kind of fall apart. I wish he would say instead, ‘Oh you can’t find a baby sitter? I’ll stay home with you.”

For whatever reason (because he isn’t paying attention, or because he sees her through his own lens) Sera’s boyfriend doesn’t seem to know how sexual she is.
“He thinks I’m very innocent,” she said. “I doubt he knows that I masturbate.”

She could have been stoned for masturbating
In case you were wondering, female circumcision, also known as genital mutilation, whereby part of a women’s vagina is removed, is practiced in Ethiopia. It’s believed to be a way to make women “better” partners by removing the clitoris, effectively making it way harder for a woman to experience pleasure and orgasm from sex.

Don’t get me started on that practice right now. My point is, Ethiopia is one of those places where there are traditions that strongly discourage female sexual pleasure or subvert them while prioritizing things like fidelity and servitude.

“In Ethiopia, I’d probably be stoned to death (for masturbating)! At least when I lived there!” she said. “They told me it was a sin.”

That probably explains why Sera didn’t start masturbating until just over two years ago, when she had already been living in the US for years and a girlfriend told her she was doing it all the time. It isn’t as satisfying for her as sex for her, but she still likes doing it.

“I like it when I’m having a bad day or when I’m bored or when my son’s asleep, or when there’s nothing on TV,” she said.

I’m really happy that Sera took her pleasure into her own hands (get it?). Because life is hard enough even with regular orgasms. I hope that she’s able to sort things out with her boyfriend or find strength in what she already knows deep down: that she is infinitely capable of striking out and taking care of herself.

Good luck, Sera. Hope you liked your new ‘do.

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Name: Jess (name has been changed)
Age: 38
From: All over (military brat), lived in California since 1999
Job: Tech Engineer
*Note: Photo is not Jess, to protect her identity. It is another trans woman who posted her photo on Pinterest and shared it on a trans resource website.

Vocab for this interview:
cis-gendered: Someone who is cool with the gender they were assigned/born with.

I’m not gonna lie here readers. Jessica stole my freakin’ heart. Male privilege? She gave it up. The vagina that most of us take for granted? She had to fight for it. Here’s her story.

For most of her life, Jessica walked through the world with the nagging feeling that something was wrong. There was this sense of discomfort in her own skin, ever present and unshakable. Inside, Jessica was a woman. But from the outside, everything about Jessica seemed like a man.

Jessica could have delved into her feelings earlier in life. But so many voices around her — from the radio talkshows her family listened to, to the preachers at the church pulpit — talked about transgendered people as off-kilter wackjobs.
Jessica absorbed these three ideas, but she simply couldn’t fit them together. Or maybe she was afraid to, because of the way she knew it would disrupt her life forever.

From Jessica: Jessica had a man’s body but felt like a woman.
From society: A man who wants to be a woman is trans.
From her conservative upbringing: Trans people are troubled and repulsive. There’s something off about them.

One day, the need to fully be the woman inside became so strong that Jessica accepted the first two ideas, and decided to continue on in spite of the third.

Jessica likes to say she was “assigned” a male gender at birth. It’s a way of de-barbing the tangled, sometimes painful story of gender for her. It’s a way of saying that she didn’t choose to be born with a penis, or grow up into man. Those things were chosen for her. Then, she chose something else.

Jessica had a good childhood in a stable home with two parents. It was what she called, “a regular, run of the mill, vanilla American family.”

But she knew at a young age that she was different from the other boys.
“I felt more comfortable around girls than I did with boys and I felt more comfortable around adult women than around adult men — for no particular reason, it just was. I frequently wanted to join the girls in their little clubhouses playing tea and house… along with playing with other things like my Transformers and my G.I. Joes. I liked both. I didn’t feel like I should have to choose.”

It wasn’t until Jessica was 35 that she came to terms with her deep feelings about her gender. Up until that point, it had been easier to push them down than to face them and confront all of the things she would have to change in order to feel right in her body.

But one day at work, while she was browsing YouTube videos, the truth all but hit her in the face.

“I like to think of it as the moment when the wool was pulled from over my eyes,” she told me.

The video slideshow showed the gradual change of a woman who was born male and transitioned into a woman over the course of two and a half years.

Before that point, Jessica had this idea that in order for a man to become a woman and pull it off, he had to start off looking feminine. The problem was, she thought she looked like a man. It just seemed impossible that she could become a woman and pull it off.

“In my mind I looked too boyish for me to pull it off. I thought there was no way I could change my appearance. Until I saw the slideshow. It showed someone who started off looking pretty masculine, then over time with hormones and surgical intervention, came out looking really feminine. And my mind was blown. My world was turned on its head.

My first reaction was: this has to be a trick. This can’t be real. There is no way someone can start looking like this and end up looking like that.”

I think that’s when I realized there was a name for how I felt. That there was an actual term and that this was not as uncommon as I thought. I believed that I was the only one. Before that, I did not believe that there were a lot of other people out there like me.”

When Jessica said this, I was thinking, really, Jessica? You lived in San Francisco. How could you not know that there were lots of other trans people around?

But she explained why.

“I think a lot of that had to do with the sheltered upbringing that I had. My parents were very conservative. I come from a fairly strict christian protestant upbringing. Some of the churches we went to were extremely conservative. And I faked it to make it, so to speak.”

“My dad used to listen to conservative talk radio in the car all the time. I was basically inundated with these neocon(servative) figures on the radio, people like Rush Limbaugh. So in my mind I had this thought, ‘Well, I’m fairly normal. And all these other (trans people), they’re not OK, there’s definitely something wrong with them. And I feel compassionate for feeling like that. But at the same time, how could I possibly have that, because I feel completely normal?’ And it just didnt make sense to me, because I didn’t feel like I was the type of person who would want to fit into the media’s portrayal — particularly the conservative media’s portrayal — of transgendered people.”

And I don’t blame Jessica. Because that portrayal is pretty damn painful.

“The internalized portrayal was that transpeople are basically dudes in a dress. They’re crossdressers and the ones that do it out in public — there’s definitely something off-kilter about them. Just not quite completely healthy. That was what I internalized from the bullshit conservative talk radio.”

After she saw the YouTube video, Jessica got curious and started researching the steps that can help a person with a male body turn it into a female body.
She learned that by suppressing testosterone and taking estrogen, your body can go through a second puberty.

“I guess that’s when my eyes were really opened to the diversity of gender and human sexual identity and presentation — all kinds of incredible things existed out there that I had never come into contact with.

That was a hell of a moment. That afternoon I was at the office in downtown San Francisco and when I saw that I broke down and started balling at my desk. It was a complicated mixture of relief, because I finally had a word or phrase to describe how I felt all this time, combined with the excitement of the fact that I had seen someone else do this.

And there was this thought: well, if they can do this, maybe I can do this.

The future of possibility was brimming in front of me, also combined with dread. What do I tell my spouse? What do I tell my family? Can I even do this and stay married? Will she stay with me? Will I lose everything? Will I get beat up for appearing “femme” even though on the outside I’m apparently masculine. There were so many different complex emotional layers.

I was completely incapacitated and was balling my eyes out. I just felt like I wanted to go home and go to bed.”

Sidenote:
What boggles my mind is this: Jessica lived in San Francisco, a mecca of sex positivity and gender fluidity for years before she had this breakthrough moment. But it was still so challenging to reconcile what she knew — that she was, at her center, good and fine and right and in a body that wasn’t the way she needed it to be — with the bigoted messages screaming in her ears that someone like her, in her truest form, was somehow innately flawed and wrong.

But for those messages, Jessica might have gotten in touch with her true nature, and drastic measures it called for, way earlier in life. She might have felt comfortable in her skin so many years earlier.

It never ceases to amaze me how we internalize messages that negate truths we absolutely know about ourselves.

After seeing that video, Jessica couldn’t go back to the way things were. She started planning for the future. But first, she needed to tell her loved ones what was going on.

Jessica started with her wife, who believed she had married a straight, cis-gendered man and had no idea that Jessica had always felt discomfort being a man.
Jessica said that her wife didn’t know just how much she disliked playing that traditional role of a man and husband.

“I think a large amount of (my frustration) had to do with me being fed up with having to perform heterosexuality and cis-normitivity. I had just gotten sick of it and so I stopped performing the ‘go getter’- type-male who pursues the female and woos her and goes on dates. Not that I don’t like doing these things, but to me it felt forced. It felt like a performance. It wasn’t something that I could do naturally, because it wasn’t in my personality. But I felt like I had to because that’s what society and my church at the time told me that was expected of me as a man.

So I had this conversation with her, prefacing it with the idea that maybe I should go talk to a therapist. I told her that I wanted to go to therapy, but not just for dealing with my emotional baggage of being married once before. I said I wanted to talk to a therapist about my gender. And I believed that I was experiencing what is called gender dysphoria.

Her initial reaction, she told me later, was revulsion. She said she felt repulsed and revolted by what she felt and terrified about what that meant for our future.

That was the beginning of a difficult few months of figuring out how I was going to break the news to people.

Jessica began telling family members about her decision to transition to a woman with a hand-written letter. She tried to communicate just how much she had thought the decision through. And how sure she was.

Most of her family members reacted with support. She wasn’t so lucky with her dad and her best friend.

My friend and I were really close. He was like my brother, but as soon as I told him, his demeanor towards me changed. It was not supportive at all.

The worst part about this was the way it dredged up the fear of loss and the feelings of judgement for Jessica. Changing her gender was already such a hard thing to do. When people she loved reacted with criticism or disgust or judgement, it made it that much harder.

“Every time someone reacted negatively, I second-guessed my decision. It just added to the emotional turmoil I was going through. A lot of people came from a place of concern, because they cared. But there were also a lot of people who thought that I wasn’t thinking this through, which to me, it’s like, I get where you’re coming from, but I’m an intelligent human being … this is something that I’ve really thought through.

Everything that was about my presentation to the world was about to change. And everyone knew that. And a lot of people were frightened for me. But also a lot of people were repulsed, because of religion, because of societal implications, because of the image and the portrayal of trans people out there.”

In those early months, everything was in a state of upheaval in Jessica’s personal life.

“There was a lot of crying and a lot of fear and a lot of hope. It was this dichotomy of positivity and negativity hand in hand. It was a really difficult time.”

It was really tough. But there were moments when the people who had loved Jessica as a man got to show her that they would also support her as a woman.

“My ex wife, God bless her heart. She tried to support me despite the fact that she is a very straight woman.

One of the first things she did was to take out clothing and see if there was clothing that I could try on to make me feel better. She let me try on one of her bras.

And I remember trying on a bra, putting on a dress and then getting in front of a mirror. And I saw myself with something that looked like a feminine figure for the first time in my life. And it was one of those moments where I just felt so overwhelmed that I just sat down on the bed and started crying.

I was just so happy to see a glimpse of what could be and what could definitely be even better once I started going further down the path. And it felt glorious. And it was terrifying and exciting and relieving at the same time.

So yeah, seeing what it felt like for me to have breasts for the first time was a really tender moment that my ex and I shared. And I’m super grateful for how hard she worked to support me. And she sat down and put her arm around my shoulder and held me close at that moment and it was really sweet.”

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Giulia is a funny, fiery, bisexual, Italian woman who was born in a small, rural town in Italy.
And Giulia is just.so.Italian. So Italian, in fact, that she managed to fit pasta into her story about the first time she masturbated.
I’m sorry but … how charming is that? More on that topic soon.

There’s no shortage of women on TV or in the media in Italy. But when Giulia was growing up, most of those sexy women were just bikini-clad, lingerie wearing, perfectly coiffed eye candy.

Giulia on the other hand, is strong, smart and independent — way more than eye candy. It’s taken a while to step into herself that way, to give herself permission to see what she wants and go get it. She said moving to America a few years ago helped.

“Growing up in Italy … the culture has more machismo. But if you’re a pretty girl, you can kind of go anywhere. If you smile and you have a pretty face, you can get anything. And everywhere, especially on TV, you always see the old men with the hot young women in their 20s.”

Since I moved to the US about six years ago, I feel like I’ve been able to let my masculinity out and gotten a lot better at making decisions and taking initiative.

I don’t feel anymore like the princess in the tower waiting for the beautiful prince to come save me.”

Taking ownership of her sexuality has been a process. Like a lot of us, innocent experimenting as a kid was sometimes tainted by messages of shame or punishment from parents or peers.

“I grew up in the countryside. We didn’t have all of the after school activities like Americans have. So sometimes after school, I would get bored and would just make sex toys from things in the house. Like pasta packages with those wide lasagna noodles.

Then, when I was done, I would feel very guilty and pray to Jesus for forgiveness.”

Sidenote: Are all you mother readers scrambling to sign your kids up for after-school soccer leagues and summer camps right about now? I hope not.
Anyway, back to the uncooked lasagna noodles.

“I also remember this time, very early, when I was just a little girl I was running around naked near my house. Because we lived in the country, we had a fire pit. I saw that the embers, still red and shouldering and decided that it might feel good to sit down with my butt on top of the them. Little kids aren’t sexual of course, they don’t know what that is. But at the same time I was discovering my body and I knew that some things felt really good.

I sat on top of the embers and my dad saw me. He got really mad and grabbed me by the hand and yanked me up. There were some other family members there and in front of them, he yelled at me and said that what I did was really bad.

I just remember feeling so ashamed at that moment.

Years later, when I was in junior high, we were talking about masturbating and this one girl confessed that she did. All of the other girls started saying that was disgusting and that only boys did that. They claimed they had never done it, but I’m sure they were. I remember feeling ashamed that I was doing it then. But all these years later I wish I could go back and tell those girls that it’s normal and good and they should do it.”

Here are some other rapid-fire questions Giulia answered for me about her sexual self.

What’s the last sex she you had?
“I haven’t had sex in two months. I needed a little bit of time after my last break up. I guess we just weren’t a perfect match. So I’ve been single for a while now. And now I think I’m finally really ready to be with someone again.”

What turns you on?
“I love dancing. I started taking salsa lessons recently. It’s so fun and it’s a way to express myself and feel loose and connected.
I’m also passionate about travel and trying new things. I love doing something that scares me at first. Then that fear turns into adrenaline.”

Who’s hot to you?
“I see myself being in a relationship with a man, but I have definitely been sexually attracted to both men and women.

When I was 12 years old, I couldn’t stop having fantasies about a friend of mine. I think she was the first one in our grade to develop breasts. I just remember going home at the end of the school day and not being able to stop thinking about her.”

What are your biggest turn ons?
“I love when someone knows how to behave in front of others. Someone who just gets in the room and knows how to make other people feel comfortable.

Physically, I also love guys with big shoulders, guys who are bigger in general. I don’t like feeling like I’m grabbing a bag of bones when I hug them.”

What are your biggest turn offs?
“I hate online dating, honestly, anything that has to do with online dating. Maybe I’m old fashioned. I just want to meet some guy in a bus station and have him give me a bouquet of roses. I tried online dating once but everyone I met, the second I spoke with them in person, I just knew that I didn’t want to do anything with them.”

What’s the worst sex you’ve ever had?
“One time, I was about to have sex with this guy. I couldn’t feel his penis, so I told him he could put it inside me. He told me that his penis was and had been inside me, and that he had already come. That was terrible.

One of the worst sex experiences I ever had happened when I met a friend of a friend in Washington D.C. We started dancing and it was really hot. At the spur of the moment, we decided to get a hotel room. So we paid, got and went up into the room and started fucking. But after 30 seconds of sex he came and then fell asleep. I felt like I had ended up with an old man when I had been expecting this hot date.

Other than that, the other bad times have happened when I’ve had great sex with someone and had so much fun, but realized that I was falling in love with them, and for them it was just about having sex. It happens.”

What’s the best sex you’ve ever had?
“I was on a camping trip in Lake Powell. I was hanging out around the camp fire with this hot guy who I had met there. We started drinking and getting excited and went into his tent. We ended up having sex — really loud sex.

Then, at some point, he went and got a friend of his, a girl, and she joined us too. It was so good because there were just no expectations, we were just flowing with the energy as it happened.

Eventually some other people from the campsite came over and told us, “Excuse me, there are other people here who are trying to rest here. I had to laugh.”

How does having good sex affect the rest of your life?
“I am in such a better mood. Like with my ex, we would be fighting about something, then we’d have sex and I would just completely forget about it.

And sex can make me feel so content. For example I can just spend a whole day in bed having sex and I don’t feel like there’s anything else I have to do.

How often do you come?
“I come pretty much every time I have sex now, unless it’s really bad sex. I know that certain movements and certain muscles get me off, so if I know the guy I’m with is about to come, I can make myself come, too. If I’m really attracted to the other person, I can just let my body take over and do it.

If you had a daughter, what would you tell her?
“If I had a daughter, I would tell her, ‘Everybody masturbates. Don’t be afraid to express your sexuality. Don’t be afraid to say what you like and don’t like.’”

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